answer ALL based on equation and quench reagent given; reaction was quenched with chosen base NaOH

e. Which species will be present in the organic layer and the aqueous layer? Draw all species below. (2 points) Organic layer contains: Aqueous layer contains: f. After the quench and separation of layers, can you separate starting material (1) and product (3) using acid base extraction? Explain why or why not. (1 point) g. After a work-up, what type of distillation method would one use to separate the product (3) from trace amounts (less than 1%) of starting material (1)? Explain thoroughly, making sure to include the concept of theoretical plates in your answer. 3 points) 3. Prelab Exercise Questions: (22 points) CASE STUDY the Pictet-Spengler Reaction! Tetrahydroisoquinolones can be synthesized in moderate yields from amines and carbonyl compounds in concentrated hydrochloric acid, as seen below. Based on this reaction, answer the following questions: HCI + . NIL H H 100C NH 2 formaldehyde 2-phenylethan -1-amine BP 195C 3 1,2,3,4-tetrahydro isoquinoline BP 235C